Hydrochloric Acid → 5-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-((1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)methyl)indolizine-8-carboxamide

HRID 1037095ノート

反応式

HRID 1037095 の反応式
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:25][C:26]1[CH:27]=[C:28]([C:34]2([C:51]([F:54])([F:53])[F:52])[O:38][N:37]=[C:36]([C:39]3[N:40]4[C:44]([C:45]([C:48](O)=[O:49])=[CH:46][CH:47]=3)=[CH:43][CH:42]=[CH:41]4)[CH2:35]2)[CH:29]=[C:30]([Cl:33])[C:31]=1[F:32].Cl.[NH2:56][CH2:57][C:58]1[CH:69]=[CH:68][C:61]2[B:62]([OH:67])[O:63][C:64]([CH3:66])([CH3:65])[C:60]=2[CH:59]=1.Cl>CC#N>[Cl:33][C:30]1[CH:29]=[C:28]([C:34]2([C:51]([F:53])([F:54])[F:52])[O:38][N:37]=[C:36]([C:39]3[N:40]4[C:44]([C:45]([C:48]([NH:56][CH2:57][C:58]5[CH:69]=[CH:68][C:61]6[B:62]([OH:67])[O:63][C:64]([CH3:66])([CH3:65])[C:60]=6[CH:59]=5)=[O:49])=[CH:46][CH:47]=3)=[CH:43][CH:42]=[CH:41]4)[CH2:35]2)[CH:27]=[C:26]([Cl:25])[C:31]=1[F:32]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86685451HCID 86685451、化合物HCID 866855275-(5-(3,5-Dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-8-carboxylic acid

生成物 1

HCID 715765255-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-((1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)methyl)indolizine-8-carboxamide

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

HATU (350 mg, 0.92 mmol) can be added to CH3CN (5 mL) at 0° C. After stirring for 5 min, the mixture can be added to a solution of 5-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-8-carboxylic acid (0.46 mmol), 5-(aminomethyl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol hydrochloride (157 mg, 0.69 mmol), and TEA (186 mg, 1.83 mmol) in CH3CN (8 mL). Then the solution can be stirred at rt for 2 h. The solution can be acidified with HCl (1 N) and extracted with EA. The combined organic layers can be washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue can be purified by prep-TLC to give the final title compound.

後処理

  1. stirringThen the solution can be stirred at rt for 2 h
  2. extractionextracted with EA
  3. washThe combined organic layers can be washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue can be purified by prep-TLC

出典と根拠

ORDレコード
ord-f57fde1e112f4daeb5b0ec7aea9ad374
出典データセット
uspto-grants-2013_10
特許番号
US08546357B2

反応ノート

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